Dimethylamine, hydrochloride → HCID 66878630, compound

HRID 1364926Notes

Reaction equation

HRID 1364926 reaction equation
Cl.[CH3:2][NH:3][CH3:4].[C:5]([O:9][C:10]([C:12]1[CH:20]=[CH:19][C:15]([C:16](O)=[O:17])=[CH:14][C:13]=1[Cl:21])=[O:11])([CH3:8])([CH3:7])[CH3:6]>C(OCC)(=O)C>[Cl:21][C:13]1[CH:14]=[C:15]([C:16](=[O:17])[N:3]([CH3:4])[CH3:2])[CH:19]=[CH:20][C:12]=1[C:10]([O:9][C:5]([CH3:8])([CH3:7])[CH3:6])=[O:11]

Participants

4

Reactant 2

HCID 10473Dimethylamine, hydrochlorideHCID 20610037HCID 20610037, compound

Product 1

HCID 66878630HCID 66878630, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

290 mg of dimethylamine hydrochloride was coupled to 1 g of 4-(tert-butoxycarbonyl)-3-chlorobenzoic acid via Procedure G. The reaction mixture was diluted with ethyl acetate, washed with 0.1 N HCl, 0.1 N NaOH and brine, dried (MgSO4) and evaporated to afford tert-butyl 2-chloro-4-(dimethylcarbamoyl)benzoate. 1.1 g of tert-butyl 2-chloro-4-(dimethylcarbamoyl)benzoate was treated with TFA (4 mL) containing trace amounts of H2O for 2 h. The reaction mixture was evaporated, and then added 0.1 N HCl. The resulting solid was filtered and washed with H2O to yield 2-chloro-4-(dimethylcarbamoyl)benzoic acid. 100 mg of 4-chloro-3-(pyridine-2-yl)aniline was coupled to 2-chloro-4-(dimethylcarbamoyl)benzoic acid via Procedure G. The product was purified on reverse phase HPLC to yield 2-chloro-N1-(4-chloro-3-(pyridin-2-yl)phenyl)-N4,N4-dimethylterephthalamide. MS (Q1) 414.1 (M)+.

Workup

  1. washwashed with 0.1 N HCl, 0.1 N NaOH and brine
  2. dry with materialdried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-76d69932256c4ec5a364519b1dd30950
Source dataset
uspto-grants-2011_02
Patent number
US07888364B2

Reaction notes

Loading…